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Group Size (2)
All listings in the United States

Awesome sailboat rentals in United States.

4.9
(8,150 Reviews)

Page 1 of 431,019 listings

Amazing Private Sailing Charter on 36' Sailboat in Marina del Rey
Sailing in Marina del Rey · 4 guests

Amazing Private Sailing Charter on 36' Sailboat in Marina del Rey

5.0
Superowner
$110-$130hour
Privat 30’ Luxury Sailing Yacht in Mazatlan Bays & Islands
Sailing in Marina Mazatlán · 8 guests

Privat 30’ Luxury Sailing Yacht in Mazatlan Bays & Islands

5.0
$135hour
 Stylishly restored classic 1970 Columbia 36 Yacht Private Sailing Tours
Sailing in Manhattan · 6 guests

Stylishly restored classic 1970 Columbia 36 Yacht Private Sailing Tours

5.0
Superowner
$240-$280hour
FUN J/105 Sailing Yacht in Downtown San Francisco, California! Up to 8 pax
Sailing in San Francisco · 8 guests

FUN J/105 Sailing Yacht in Downtown San Francisco, California! Up to 8 pax

5.0
Superowner
$250-$300hour
Beautiful sailboat hunter 40ft adventure sea breezes in Puerto Vallarta
Sailing in Marina Vallarta · 13 guests

Beautiful sailboat hunter 40ft adventure sea breezes in Puerto Vallarta

4.8
$87hour
New  Catamaran Lagoon 450 Charter in Puerto Vallarta Mexico
Events in Marina Vallarta · 30 guests

New Catamaran Lagoon 450 Charter in Puerto Vallarta Mexico

4.9
Superowner
Best of 2023
$350hour
⛵New in the bay! Lagoon 42 Yacht Catamaran in La Cruz
Sailing in La Cruz de Huanacaxtle · 20 guests

⛵New in the bay! Lagoon 42 Yacht Catamaran in La Cruz

5.0
Superowner
Best of 2023
$250-$325hour
Luxury 48' Leopard Catamaran in Cartagena
Sailing in Cartagena · 25 guests

Luxury 48' Leopard Catamaran in Cartagena

4.8
Superowner
Best of 2023
$200hour
41' Beautiful sailing catamaran, perfect for lounging, swimming, and sailing
Sailing in Sag Harbor · 6 guests

41' Beautiful sailing catamaran, perfect for lounging, swimming, and sailing

5.0
$450-$500hour
Instant Book
Sunset Sails: Explore the Open Waters of Tampa, Florida
Sailing in Tampa · 6 guests

Sunset Sails: Explore the Open Waters of Tampa, Florida

5.0
$160hour
Beautiful Sea Ray Flybridge 45 ft Available In Cabo San Lucas,
Events in Marina · 12 guests

Beautiful Sea Ray Flybridge 45 ft Available In Cabo San Lucas,

5.0
$350hour
Spacious, fast 80 foot sailboat with a hot tub
Events in Marina Vallarta · 40 guests

Spacious, fast 80 foot sailboat with a hot tub

5.0
$275hour
Great Sailing Catamaran for up to 25 people!
Sailing in Cartagena · 25 guests

Great Sailing Catamaran for up to 25 people!

5.0
Superowner
Best of 2023
$1,250day
40' Leopard Luxury Catamaran All-Inclusive Charter in Riviera Maya.
Sailing in Puerto Aventuras · 20 guests

40' Leopard Luxury Catamaran All-Inclusive Charter in Riviera Maya.

5.0
Superowner
Best of 2023
$450hour
All Inclusive Sunset Party Cruise in Cabo San Lucas!
Tours in Marina · 45 guests

All Inclusive Sunset Party Cruise in Cabo San Lucas!

5.0
$281hour
MAUI CATAMARAN - ISLANDS, SUNSETS AND NIGHT EVENTS
Sailing in Cartagena · 40 guests

MAUI CATAMARAN - ISLANDS, SUNSETS AND NIGHT EVENTS

5.0
Superowner
Best of 2023
$1,100day
46 feet luxury yacht in Montego Bay with round trip transportation!
Powerboats in Montego Bay · 16 guests

46 feet luxury yacht in Montego Bay with round trip transportation!

5.0
Best of 2023
$699hour
FOLLY BEACH CATAMARAN SUNSET SAIL, departing Folly River boat landing 190/hr
Sailing in Folly Beach · 6 guests

FOLLY BEACH CATAMARAN SUNSET SAIL, departing Folly River boat landing 190/hr

5.0
$175person
30ft Catlina Sailboat Charter in Alameda CA
Sailing in Alameda · 6 guests

30ft Catlina Sailboat Charter in Alameda CA

5.0
$95hour
Luxury Fountaine Pajot 61 feet in Flamingo
Events in Tamarindo · 20 guests

Luxury Fountaine Pajot 61 feet in Flamingo

5.0
$2,000day
22ft Pontoon Suntracker Party Barge DLX 10 people in Bay Pines. Gas included!
Powerboats in Bay Pines · 10 guests

22ft Pontoon Suntracker Party Barge DLX 10 people in Bay Pines. Gas included!

4.7
Superowner
$49hour
38' Luxury Catamaran All-Inclusive Cruise in Riviera Maya.
Sailing in Puerto Aventuras · 15 guests

38' Luxury Catamaran All-Inclusive Cruise in Riviera Maya.

5.0
Superowner
Best of 2023
$420hour
40' Luxury Catamaran in Cozumel
Sailing in San Miguel de Cozumel · 20 guests

40' Luxury Catamaran in Cozumel

5.0
Superowner
$290hour
😍Experience Peace and Tranquility 😍🍷🍾
Sailing in Coronado · 4 guests

😍Experience Peace and Tranquility 😍🍷🍾

5.0
$100hour

Sailing Reviews in United States

  1. RW

    Ronnie

    FOLLY BEACH CATAMARAN SUNSET SAIL, departing Folly River boat landing 190/hr

    Johnny, thanks so much for the trip. Although we have been in the waters around Folly many times over the years, we had never been on a catamaran. It was awesome! We saw so much in just 2 hours! Baby stingray swimming by about 2 feet away, countless dolphins playing and splashing in the water,me stepping on a huge blue crab (that scared me to death! lol!) to my first EVER sighting of a live logger head turtle right by the boat… it was absolutely incredible. Oh, forgot to mention the sea shell my wife found (as big as my hand). Thank you for a great trip!

  2. KM

    Katelyn

    30ft Catlina Sailboat Charter in Alameda CA

    From a few hours of sailing with Bradford we could easily tell he was an experienced and passionate captain. Our charter was extremely hands on and educational, as we requested! My partner has always been curious about sailing and walked away with a wealth of knowledge Bradford was kind, funny, and pleasant to spend hours out at sea with- highly recommend to anyone considering booking a trip- we have already begun referring him to friends and family :)

  3. KO

    Kimberly

    All Inclusive Sunset Party Cruise in Cabo San Lucas!

    We had the best experience with Ismael and team! The entire staff aboard the boat went above and beyond. Sergio paddled out to the beach to bring us drinks, Andrea jumped into the water with her GoPro to capture amazing pictures, they made me a birthday cake in the shape of a K, and showed us all around the bay and the pacific. I would recommend them and hope to rebook myself!

  4. LW

    Lauren

    Amazing Private Sailing Charter on 36' Sailboat in Marina del Rey

    This was the perfect sail for my dad's birthday. Matthew was extremely responsive in his communications, made us feel very comfortable on his boat, and even let my dad do as much of the sailing as he wanted (which made my dad's day!). Matthew was great company, the boat was beautiful, and the winds were ideal (we let Matthew choose the time of day for the best sailing conditions). Thank you, Matthew, for helping make this one of the best birthdays for my dad. It was such a fun and special adventure!

  5. EN

    Eva

    FUN J/105 Sailing Yacht in Downtown San Francisco, California! Up to 8 pax

    Our group had an absolutely fantastic experience on the sailboat tour! Drew was knowledgeable and friendly and pointed out points of interest on our tour of the bay. The views were amazing and we saw lots of interesting wildlife – highly recommend!

  6. ME

    Margaret

    ⛵New in the bay! Lagoon 42 Yacht Catamaran in La Cruz

    Our group had the best time on this boat!!! It was absolutely fabulous and the crew was outstanding. The boat was super clean and spacious and the crew seemed to have literally thought of everything and seemed very knowledgeable, we were spoiled! I highly recommend!